Alphabetical ordering

The paragraphs below are arranged in alphabetical order and are intended only as a short reference. For readers interested in a particular topic a few references are given which serve as a link for further reading. Generally, it should be noted that the separation of the categories below is to a large extent based on historic evolution rather than physicochemical mechanisms. 

The elements in Group II of the Periodic Table (alkaline earth metals) are. in alphabetical order, barium (Ba). beryllium (Be), calcium (Ca). magnesium (Mg), radium (Ra) and strontium (Sr). 

In empirical formulas of inorganic compounds, electropositive elements are listed first [3]. The stoichiometry of the element symbols is indicated at the lower right-hand side by index numbers. If necessary, the charges of ions are placed at the top right-hand side next to the element symbol (e.g., S "). In ions of complexes, the central atom is specified before the ligands are listed in alphabetical order, the complex ion is set in square brackets (e.g., Na2[Sn(OH)+]). 

The elements of an organic compound are listed in empirical formulas according to the Hill system [8] and the stoichiometry is indicated by index numbers. Hill positioned the carbon and the hydrogen atoms in the first and the second places, with heteroatoms following them in alphabetical order, e.g., C9H11NO2. However, it was recognized that different compounds could have the same empirical formula (see Section 2.8.2, on isomerism). Therefore, fine subdivisions of the empirical... 

Molecular formulas of organic compounds are customarily presented in the fashion C2H5Br02 The number of carbon and hydrogen atoms are presented first followed by the other atoms in alphabetical order Give the molecular formulas corresponding to each of the compounds in the preceding problem Are any of them isomers ... 

The compound becomes an octane derivative that bears a C 3 methyl group and a C 4 ethyl group When two or more different substituents are present they are listed m alphabetical order in the name The lUPAC name for this compound is 4 ethyl 3 methyloctane... 

List the substituents attached to the longest con tinuous chain in alphabetical order Use the pre fixes di- tri- tetra- and so on when the same substituent appears more than once Ignore these prefixes when alphabetizing... 

When two or more different substituents are pres ent list them in alphabetical order and number the ring in the direction that gives the lower num ber at the first point of difference... 

List the substituents attached to the basis group in alphabetical order using replicating prefixes when necessary... 

Substitutive lUPAC nomenclature names epoxides as epoxy derivatives of alkanes According to this system ethylene oxide becomes epoxyethane and propylene oxide becomes 1 2 epoxypropane The prefix epoxy always immediately precedes the alkane ending it is not listed m alphabetical order like other substituents... 

Ethers are named m substitutive lUPAC nomenclature as alkoxy derivatives of alkanes Functional class lUPAC names of ethers are derived by listing the two alkyl groups m the general structure ROR m alphabetical order as separate words and then adding the word ether at the end When both alkyl groups are the same the prefix di precedes the name of the alkyl group... 

Section 16 1 Ethers are compounds that contain a C—O—C linkage In substitutive lUPAC nomenclature they are named as al/coxy derivatives of alkanes In functional class lUPAC nomenclature we name each alkyl group as a separate word (m alphabetical order) followed by the word ether... 

Ketones may also be named using functional class lUPAC nomenclature by citing the two groups attached to the carbonyl m alphabetical order followed by the word ketone Thus 3 methyl 2 butanone (substitutive) becomes isopropyl methyl ketone (functional class)... 

In naming carboxylic acid anhydrides in which both acyl groups are the same we simply specify the acid and replace acid by anhydride When the acyl groups are dif ferent they are cited m alphabetical order... 

Aniline is the parent lUPAC name for ammo substituted derivatives of benzene Substituted derivatives of aniline are numbered beginning at the carbon that bears the ammo group Substituents are listed m alphabetical order and the direction of number mg IS governed by the usual first point of difference rule... 

An old name for benzene was phene and its hydroxyl derivative came to be called phe nol This like many other entrenched common names is an acceptable lUPAC name Likewise o m and p cresol are acceptable names for the various ring substituted hydroxyl derivatives of toluene More highly substituted compounds are named as deriv atives of phenol Numbering of the ring begins at the hydroxyl substituted carbon and proceeds m the direction that gives the lower number to the next substituted carbon Sub stituents are cited m alphabetical order... 

Molecular formula (Section 1 7) Chemical formula in which subscnpts are used to indicate the number of atoms of each element present in one molecule In organic compounds carbon is cited first hydrogen second and the remaining el ements in alphabetical order... 

If the same alkyl group occurs more than once as a side chain, this is indicated by the prefixes di-, tri-, tetra-, etc. Side chains are cited in alphabetical order (before insertion of any multiplying prefix). The name of a complex radical (side chain) is considered to begin with the first letter of its complete name. Where names of complex radicals are composed of identical words, priority for citation is given to that radical which contains the lowest-numbered locant at the first cited point of difference in the radical. If two or more side chains are in equivalent positions, the one to be assigned the lowest-numbered locant is that cited first in the name. The complete expression for the side chain may be enclosed in parentheses for clarity or the carbon atoms in side chains may be indicated by primed locants. 

Isomers are distinguished by lettering the peripheral sides of the parent beginning with a for the side 1,2, and so on, lettering every side around the periphery. If necessary for clarity, the numbers of the attached position (1,2, for example) of the substituent ring are also denoted. The prefixes are cited in alphabetical order. The numbers and letters are enclosed in square brackets and placed immediately after the designation of the attached component. Examples are... 

Systematic names formed by applying the principles of substitutive nomenclature are single words except for compounds named as acids. First one selects the parent compound, and thus the suffix, from the characteristic group listed earliest in Table 1.7. All remaining functional groups are handled as prefixes that precede, in alphabetical order, the parent name. Two examples may be helpful ... 

Prefixes and Affixes. Prefixes are arranged alphabetically and placed before the parent name multiplying affixes, if necessary, are inserted and do not alter the alphabetical order already attained. The parent name includes any syllables denoting a change of ring member or relating to the structure of a carbon chain. Nondetachable parts of parent names include... 

Acid Anhydrides. Symmetrical anhydrides of monocarboxylic acids, when unsubstituted, are named by replacing the word acid by anhydride. Anhydrides of substituted monocarboxylic acids, if symmetrically substituted, are named by prefixing bis- to the name of the acid and replacing the word acid by anhydride. Mixed anhydrides are named by giving in alphabetical order the first part of the names of the two acids followed by the word anhydride, e.g., acetic propionic anhydride or acetic propanoic anhydride. Cyclic anhydrides of polycarboxylic acids, although possessing a... 

Sulfonium Compounds. Sulfonium compounds of the type R R R S X are named by citing in alphabetical order the radical names followed by -sulfonium and the name of the anion. For heterocyclic compounds, -ium is added to the name of the ring system. Replacement of > CH by sulfonium sulfur is denoted by the prefix thionia-, and the name of the anion is added at the end. 

Sulfoxides. Sulfoxides, R — SO—R, are named by placing the names of the radicals in alphabetical order before the word sulfoxide. Alternatively, the less senior radical is named followed by sulfinyl- and concluded by the name of the senior group. For example, CH3CH2—SO—CH2CH2CH3 is named either ethyl propyl sulfoxide or l-(ethylsulfinyl)propane. 

Placement of Atoms in a Formula. The electropositive constituent (cation) is placed first in a formula. If the compound contains more than one electropositive or more than one electronegative constituent, the sequence within each class should be in alphabetical order of their symbols. 

The alphabetical order may be different in formulas and names for example, NaNH4HP04, ammonium sodium hydrogen phosphate. 

Isotopically Labeled Compounds. The hydrogen isotopes are given special names H (protium), H or D (deuterium), and H or T (tritium). The superscript designation is preferred because D and T disturb the alphabetical ordering in formulas. 

Naming a Coordination Compound. To name a coordination compound, the names of the ligands are attached directly in front of the name of the central atom. The ligands are listed in alphabetical order regardless of the number of each and with the name of a ligand treated as a unit. Thus diammine is listed under a and dimethylamine under d. The oxidation number of the central atom is stated last by either the oxidation number or charge number. 

The names of addition compounds are formed by connecting the names of individual compounds by a dash (—) and indicating the numbers of molecules in the name by Arabic numerals separated by the solidus (diagonal slash). All molecules are cited in order of increasing number those having the same number are cited in alphabetic order. However, boron compounds and water are always cited last and in that order. 

Although these professional-use-only products do not require ingredient labeling, the cosmetics industry has developed a program to voluntarily Hst the components of professional products. However, under this voluntary program, the ingredients are Hsted in alphabetical order rather than descending order. This has been done to make it easier for the professional hairdresser to locate a specific compound that may be of interest. 

Negatively coordinated groups are given before neutral coordinated groups in the examples of Werner scheme names above. Ewens and Bassett presented good reasons why that order should be reversed. The lUPAC rules (20) recommend that ligands be cited in alphabetical order regardless of their... 

Symmetrical diaLkyl peroxides are commonly named as such, eg, dimethyl peroxide. For unsymmetrical diaLkyl peroxides, the two radicals usually are hsted ia alphabetical order, eg, ethyl methyl peroxide. For organomineral peroxides or complex stmctures, ie, where R and R are difficult to name as radicals, the peroxide is named as an aLkyldioxy derivative, although alkylperoxy is stUl used by many authors. CycHc peroxides are normally named as heterocychc compounds, eg, 1,2-dioxane, or by substitutive oxa nomenclature, eg, 1,2-dioxacyclohexane however, when the two oxygens form a bridge between two carbon atoms of a ring, the terms epidioxy or epiperoxy are frequendy used. The resulting polycycHc stmcture has been called an endoperoxide, epiperoxide, or transaimular peroxide. 

C. Tomlin, ed.. The Pesticides Manual A World Compendium, Incorporating the Agrochemicals Handbook, 10th ed.. The British Crop Protection Council and The Royal Society of Chemistry, Crop Protection PubHcations, Cambridge, U.K., 1994. Includes 725 entries by common name in alphabetic order, with chemical stmcture, chemical name(s), molecular formula, CAS Registry Number, physicochemical properties, commercialisation, mode of action, uses, trade names, analytical methods, mammalian toxicology, ecotoxicology, and environmental fate. 

Quaternary ammonium compounds are usually named as the substituted ammonium salt. The anion is Hsted last (3). Substituent names can be either common (stearyl) or lUPAC (octadecyl). If the long chain in the compound is from a natural mixture, the chain is named after that mixture, eg, taHowalkyL Prefixes such as di- and tri- are used if an alkyl group is repeated. Complex compounds usually have the substituents Hsted in alphabetical order. Some common quaternary ammonium compounds and their appHcations in patent Hterature are Hsted in Table 1. 

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